Visible light-induced sulfonylation with sulfinates as closed-shell radical acceptors

By: Hu, Dongyan ; Shen, Lei; Chaw, Su Su Htwe ; Liang, Kangjiang; Xia, Chengfeng

Organic Chemistry Frontiers

DOI：https://doi.org/10.1039/d4qo00370e

Published：2024-APR

Abstract

      (Hetero)aryl sulfones possess wide biological activities and serve as important structural motifs in pharmaceuticals and agrochemicals. Sulfinates are important radical precursors, via oxidation, for sulfonylation, but suffer from strong oxidative conditions as well as instability of sulfonyl radical intermediates. Herein, we find that sulfinates can serve as closed-shell radical acceptors instead of radical precursors for the subsequent sulfonylation, enabling the sulfonylation under reductive conditions rather than oxidative conditions. A photochemical sulfonylation was developed by coupling aryl halides with aryl/alkyl sulfinates in a redox-neutral manner. This newly developed sulfonylation method provides a versatile platform for the synthesis of diverse (hetero)aryl sulfones under mild conditions and shows broad substrate scope and synthetically important functional-group tolerance.

      Sulfinates as close-shell radical acceptors instead of radical precursors for redox-neutral photochemical sulfonylation.